Synthesis and leishmanicidal activity of cinnamic acid esters: structure–activity relationship
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Other documents of the author: Otero, Elver; Robledo, Sara M.; Diaz-Oltra, Santiago; Carda, Miguel; Muñoz, Diana; Paños Pérez, Julián; Vélez, Iván D.; Cardona Galeano, Wilson Isidro
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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Title
Synthesis and leishmanicidal activity of cinnamic acid esters: structure–activity relationshipAuthor (s)
Date
2014Publisher
SpringerISSN
1054-2523; 1554-8120Bibliographic citation
OTERO, Elver, et al. Synthesis and leishmanicidal activity of cinnamic acid esters: Structure–activity relationship. Medicinal Chemistry Research, 2014, vol. 23, no 3, p. 1378-1386.Type
info:eu-repo/semantics/articlePublisher version
http://link.springer.com/article/10.1007%2Fs00044-013-0741-ySubject
Abstract
Several cinnamic acid esters were obtained via Fischer esterification of cinnamic acids derivatives with aliphatic alcohols. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds ... [+]
Several cinnamic acid esters were obtained via Fischer esterification of cinnamic acids derivatives with aliphatic alcohols. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes and cytotoxic activity was evaluated against mammalian U-937 cells. The compounds 11, 15–17, and 23, were active against Leishmania parasite and although toxic for mammalian cells, they still are potential candidates for antileishmanial drug development. A SAR analysis indicates that first, while smaller alkyl chains lead to higher selectivity indices (10, 11 vs. 12–17); second, the degree of oxygenation is essential for activity, primarily in positions 3 and 4 (17 vs. 18–20 and 22); and third, hydroxyl groups increase both activity and cytotoxicity (14 vs. 23). On the other hand, the presence of a double bond in the side chain is crucial for cytotoxicity and leishmanicidal activity (12 vs. 21). However, further studies are required to optimize the structure of the promising molecules and to validate the in vitro activity against Leishmania demonstrated here with in vivo studies. [-]
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Medicinal Chemistry Research, 2014, vol. 23, no 3Rights
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